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GCE-AS-A2-IB ADVANCED LEVEL ORGANIC CHEMISTRY The Structure and Nomenclature (naming) of the homologous series of ALCOHOLS of general formula CnH2n+1OH (and some isomeric ethers) Part 1 Allow time for graphic images/diagram/pictures to download © Dr W P Brown Examples of displayed formula, graphic formula, molecular formula, skeletal formula, structural formula including isomers of molecular formula up to C7H16O, lower ETHER (alkoxyalkanes) functional group isomers and epoxyalkanes Examples of 1b chloroalcohols, 2. Diols/triols, 3. Cyclo-alcohols, 4. Phenols, 5. Epoxy compounds organic chemical id tests * Summary of functional groups m/c quiz naming alcohols/ethers * type in name quiz on alcohols/ethers A brief guide to alcohol, ether and epoxy-alkane structure-naming-nomenclature
1a Aliphatic alcohols CnH2n+1OH (and isomeric ethers) (1) The simplest alcohol is methanol
(prim)
(methyl alcohol), molecular formula of (a) and four structural formulae representations: (b) the latter gives a 3-dimensional structural formula impression of the molecule. NOTES: (1) all the C-C-H, H-C-H, C-O-H, C-C-O or H-C-O bond angles are all approximately 109 degrees in all the non-cyclic alcohols or alkanols shown here or below. (2) From (b), the most 'shortened' structural formula, to (d), the most detailed structural formula, show increasing detail of the specific bonds and spatial arrangement of the atoms. (3)The naming of alcohols is based on the longest carbon chain and the suffix 'ol' meaning the functional group -OH (hydroxyl) attached to the carbon chain. (2) The next alcohol is ethanol
(prim) (ethyl
alcohol, 'alcohol'), molecular formula (a) five structural formulae representations (b) NOTE: The skeletal formula is that of ethane plus the -OH, so the bond between the carbon chain and the hydroxyl group is shown in the skeletal formula - do NOT confuse it with a 'propane skeleton' - watch out for this in alcohols, ethers and any other structures where a H atom is replaced by a group that is NOT alkyl. The skeletal formula usually represents the bond network /\/ etc. apart from the C-H bonds.
(3) With the molecular formula (a)
There are two structural (position) isomers of alcohols/alkanols of molecular formula (4) Propan-1-ol (prim) (1-propanol, n-propanol, n-propyl alcohol) has the structural formulae (a) or (d) NOTE a suffix number is now needed to show the position of the -OH or 'ol' functional group.
(5) Propan-2-ol (sec) (2-propanol, isopropanol, isopropyl alcohol) has the structural formulae (a) (d)
(6) There is one ether functional group structural isomer with the molecular formula (a) (b) (e)
There are four structural isomers of (7) Butan-1-ol (prim) (1-butanol, n-butanol, n-butyl alcohol), shortened structural formulae (a) and the skeletal formula is (c)
(8) Butan-2-ol (sec) (2-butanol, sec-butyl alcohol, shortened structural formulae (a) or (b)
(9) 2-methylpropan-1-ol (sec) (isobutyl alcohol, isobutanol), shortened structural formulae (a)
(10) 2-methylpropan-2-ol (tert) (tert-butyl
alcohol), shortened structural formulae (a) or (b)
There are three isomeric ethers, isomeric with the alcohols of molecular formula
(11) ethoxyethane (diethyl ether,
'ether'), structural formulae (a)
(12) 1-methoxypropane (use of prefix number now required), shortened structural formulae (a)
(13) 2-methoxypropane, shortened structural formula (a)
There are 8 isomeric alcohols derived from the molecular formula (14) pentan-1-ol (1-pentanol, n-pentanol,
n-pentyl alcohol, n-amyl alcohol), , shortened structural formula (a)
(15) pentan-2-ol, shortened structural formula (a)
(16) pentan-3-ol, shortened structural formula (a)
(17) 2-methylbutan-1-ol ('active' amyl
alcohol), shortened structural formula (a)
(18) 3-methylbutan-1-ol (isopentanol,
isoamyl alcohol), shortened structural formula (a)
(19) 2-methylbutan-2-ol (t-amyl alcohol,
t-pentanol), shortened structural formula (a)
(20) 3-methylbutan-2-ol, shortened structural formula (a)
(21) 2,2-dimethylpropan-1-ol (neopentyl
alcohol), shortened structural formula (a)
There are 6 isomeric ethers, also isomeric with the above 8 alcohols derived from the molecular formula (22) 1-methoxybutane, shortened structural formula (a)
(23) 2-methoxybutane, shortened structural formula (a)
(24) 1-ethoxypropane, shortened structural formula (a)
(25) 2-ethoxypropane, shortened structural formula (a)
(26) 1-methoxy-2-methylpropane, shortened structural formula (a)
(27) 2-methoxy-2-methylpropane, shortened structural formula (a)
There are 17 isomeric alcohols derived from the molecular formula (28) hexan-1-ol, shortened structural formula (a)
(29) hexan-2-ol, shortened structural formula (a)
(30) hexan-3-ol, shortened structural formula (a)
(31) 2-methylpentan-1-ol, shortened structural formula (a)
(32) 3-methylpentan-1-ol, shortened structural formula (a)
(33) 4-methylpentan-1-ol, shortened structural formula (a)
(34) 2-methylpentan-2-ol, shortened structural formula (a)
(35) 3-methylpentan-2-ol, shortened structural formula (a)
(36) 4-methylpentan-2-ol, shortened structural formula (a)
(37) 2-methylpentan-3-ol, shortened structural formula (a)
(38) 3-methylpentan-3-ol, shortened structural formula (a)
(39) 2,2-dimethylbutan-1-ol, shortened structural formula (a)
(40) 2,3-dimethylbutan-1-ol, shortened structural formula (a)
(41) 3,3-dimethylbutan-1-ol, shortened structural formula (a)
(42) 2,3-dimethylbutan-2-ol, shortened structural formula (a)
(43) 3,3-dimethylbutan-2-ol, shortened structural formula (a)
(44) 2-ethylbutan-1-ol (name does not fit in with longest carbon chain rule, but a logical name to use), shortened structural formula (a)
1b Examples of aliphatic 'chloroalcohols' 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. AS A2 AQA Edexcel OCR Nuffield Salters WJEC CCEA IB Advanced Level Chemistry at Doc Brown's Chemistry Clinic: Science-chemistry for revising course content for learning teaching tutoring e.g. revision notes on Molecular Structure and Nomenclature of alcohols/alkanols and ethers and their derivatives graphic formula of alkanols alcohols and ethers skeletal formula structural formula molecular formula word equations balanced symbol equations structure formula/formulae annotated/labelled diagrams apparatus information methods of preparation described properties defined explained facts data concepts principles theory explanation descriptive/descriptions definitions revision notes for Molecular Structure and Nomenclature/naming of alcohols and ethers and their derivatives graphic alcohols/alkanols and ethers skeletal formula structural formula molecular formula, tests and multiple choice quizzes for Molecular Structure and Nomenclature/naming of alcohols and ethers and their derivatives graphic alcohols and ethers skeletal formula structural formula molecular formula, worksheets for Molecular Structure and Nomenclature of alcohols/alkanols and ethers and their derivatives graphic alcohols and ethers skeletal formula structural formula molecular formula, practice questions for Molecular Structure and Nomenclature of alcohols and ethers and their derivatives graphic alcohols and ethers skeletal formula structural formula molecular formula covering: AQA Advanced Subsidiary AS Chemistry Advanced A2 Chemistry, CCEA Advanced Subsidiary AS Chemistry Advanced A2 Chemistry, Edexcel Advanced Subsidiary AS Chemistry Advanced A2 Chemistry, OCR Advanced Subsidiary AS Chemistry Advanced A2 Chemistry, WJEC Advanced Subsidiary AS Chemistry Advanced A2 Chemistry, IB Advanced Chemistry, CIE Cambridge International Advanced Chemistry, SQA Scottish and Irish Higher Certificate Chemistry, I know quite a few teachers find the site helpful revision for 'professional development' of their teaching as well as their students revision of Molecular Structure and Nomenclature of alcohols and ethers and their derivatives graphic alcohols and ethers skeletal formula structural formula molecular formula. However I DO NOT DEAL IN PAST EXAM PAPERS - you get them from the examination board or your school/college teacher, not from Doc Brown's Chemistry Clinic! AS A2 AQA Edexcel OCR Nuffield Salters WJEC CCEA IB Advanced Level Chemistry * Copyright © Dr W P Brown 2000-2008 All rights reserved including the revision notes pages, quizzes, worksheets etc. * Doc Brown's Chemistry Clinic * www.docbrown.info/ *
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